How I Lost My Cherry

by Leslie Schmidt

Note: With the changes of some names, this is the story of how I lost my cherry when I was 16 with my best friend's 11 year old sister.

This happened a long time ago, when I was 16—ancient history. It is the story of how I lost my virginity back in the early '70's, the time before Reagan, when it was still legal to have fun in America, the days of Sex, Drugs, and Rock and Roll. Also, because of the more sensible laws of that era (what was it I said about it being legal to have fun?), nothing that happened was illegal (or wrong for that matter).

It was the beginning of 10th grade. Because of a childhood illness (rheumatic fever), I had started school a year late, so I had turned 16 at the end of the 9th grade and had gotten my drivers license over the summer. My best friend was, of course, 15, and actually a bit young for his grade, having just turned 15 in June. (Another strange detail—because they had lived in Holland when they were younger, both Gary and Bridgett were a grade ahead of others their age when they moved to the US in 1966.)

This was when Middle School was called Junior High School and it ran from 7th to 9th grades, so we were both newbies at the High School. My friend, Gary, had developed a summer romance with a girl who was still at the Junior High (9th grade) and their mothers had begun to get tired of chauffeuring them around on dates. So one day Gary's mother called my mother (they were good friends too) and asked if I could drive them around—our mothers arranged for us to do double dates (usually in their yellow VW Squareback).

There was a problem, however, at the time I didn't have a girlfriend. I'm not sure how it was arranged but the problem was solved by the addition of Gary's eleven year old sister, Bridgett. Actually, this was fine with me, Gary and I had grown up together as best friends and, of course, Bridgett had always been around—she never made herself a pest at all and actually joined us sometimes when we climbed around on the woods or played with models or GI Joe. So Gary, his girlfriend Margret, Bridgett and me actually became a regular foursome at the local movie theatres, Mac Donald's, even at the Junior High dances (although we skipped the Homecoming dance at the High School, went to see a movie instead.) I never got any ribbing from other guys about dating a 7th grader, it seemed to be understood that it was all done so Gary and Margret could go out, Bridgett and I really weren't dating. For Bridgett it must have been a hoot to go to the Junior High dances with a High School guy, even if he did drive her mother's car.

Now, of course, what Gary's mother didn't know was that Gary and Margret were fucking like rabbits. I was in early on this because I had gotten a summer job stocking shelves at a local drug store and was Gary's main source of rubbers. At first I lifted them but, after a couple of boxes of Trojan-Eze had disappeared I started buying them. The pharmacist, Phil, probably thought he was doing a public service keeping the young ladies of the community out of the Home for Unwed Mothers. (These days teenage girls just bring their kids home and dump them on the grandparents).

So, from July through the fall, Gary and Margret were using up a couple of one dozen boxes a week—I'm not sure where he got the money at $3.47 a box.

Now, understand, Gary and Margret were completely unabashed about what they were doing. I still remember Bridget turning bright red in Mac Donald's once when Margret made some sexual comment I don't remember. Then, probably on our third or fourth time out, we had gone for a hike along the C & O Canal near Great Falls. On the way back, they put the back seat down in the VW and were going at it as we bounced down the “Rock Creek Rollercoaster” part of the DC Beltway. I watched them in the rear view mirror while trying to drive and Bridget sat in the right seat and looked embarrassed. Eventually she started to giggle as Margret's “Oh, oh, oh”s got a bit loud. It was night but, still, I'm sure that people behind us could have seen Gary's ass bouncing up and down, and Margret's feet up on the roof of the car.

Of course, at some point I cuddled up with Bridget during a movie and I was really surprised when her tongue met mine pretty much the first time we kissed. It was probably later in the same movie that I rubbed her training bra with my thumb and the palm of my hand. Again, it's too far back in the foggy past to remember the specifics but I do remember that we were in her parents family room the first time I worked my hand down her pants and got her off finger fucking her. It wasn't until months later, with a girl closer to my age, that I realized that she didn't have any hair and that that was...well...not normal for when you're finger fucking (unless, of course, you're finder fucking an eleven year old). It was also that same evening in the family room that she rubbed my cock through my jeans and I slimed up my hip, then had to get into the bathroom to clean up the mess before it soaked completely through my pants.

The first time we ever saw each other naked had to have been in September, because it was still warm. My family had a sailboat (a Rhodes 19 daysailor) that we kept on the Chesapeake Bay. One afternoon the four of us went sailing and Gary talked Margret into taking her top off. Bridget was in a one piece and, after some ribbing from the older girl, pulled the top of her suit down. Of course, Gary dared me and we quickly lost our trunks into the bilge, much to the amusement of Margret and the embarrassment of Bridget. As it was, Bridget finally rolled her eyes and said 'OK' when she finally pulled her suit completely off to join the rest of us in getting an all over tan. We were actually naked for only a few minutes before a flotilla of other sailboats from the Naval Academy was overtaking us and the girls insisted on getting dressed again.

Well, while I've got their clothes off, let me describe the girls to you. First Margret:

Margret was, as I've said, fourteen at the time, and she was a fully developed and (as I now would say) absolutely lovely young woman. She was just around five feet tall, maybe as much as 5'3”, probably around 115 pounds. She was not fat but definitely 'shapely'. She was somewhere between a B and a C cup, probably 34” or 35” with hips to match and a waist that gave her a nice hourglass figure. Her nipples were large, pencil erasers sticking out from half-dollar size aureoles that themselves were cones, giving her nicely pointed breasts. There was a small crease under each tit (no problem with the 'pencil test') a flat but not muscular stomach, shapely thighs with a nice triangle of dark curls at their meeting. She wore her hair short, not reaching her shoulders, dark, almost black, and wavy, bangs across her wide forehead, lovely cheeks, straight nose and a full-lipped mouth.

She had a personality to go with her looks—smart, outgoing, and a biting sense of humor. Yes, sarcasm was just one of the services provided. Did I mention that she was a JAP ? (Jewish-American Princess) She had no trouble telling you what she thought and made fun of people unmercifully. She was a lot of fun to be around, Gary had quite a catch. But then again, she'd be (and was) a tough one to hold on to. Now for Bridget:

As I said, she was eleven, soon to be twelve just after New Years. Frankly, and I don't want to be mean at all here, but she was rather ordinary looking. She also had dark hair, but it was straight and reached down to her shoulder blades. She had bangs that went straight across her forehead just at her eyebrows. Her face was pleasant but it would never be called pretty. It was just a little narrow, dark eyes, a narrow nose and small mouth. She was very quiet, keeping her comments to herself, didn't talk bad about others, not picky about what she ate or wore. She also lived up to her reputation for being really smart and a book worm. Her shoulders were narrow, her nipples just bumps on dime size aureoles that were just beginning to be lifted on very slight swellings.

She had almost no fat, her arms were skinny and her legs just barely avoided the same description. Her hips were a little wide for her proportions, she was long waisted. She was maybe getting just to five feet but I'm sure she was well shy of 100 pounds. Unlike Margret, her pussy was still a girl's. She had long, thin pussy lips and there was no sign of any hair. Her clit ridge peeked out from between her lips.

I've said that she was quiet, and to this day I cannot say that I knew her well (I mean personality, not the biblical 'know'). Still, I'm sure that she didn't do anything she didn't want to do. If she didn't want to do something she'd just shake her head and that was that. The expression carried enough of a message to tell you that you wouldn't change her mind. Still, simply because of this, I'm sure that she wanted to be with me because, I'm quite sure, she wouldn't have if she didn't want to. Also, although she wasn't aggressive, she certainly didn't avoid getting it on.

At the time, I was too stupid to see what a great thing I had going. Today, she's the kind of image I keep in my mind; then, I was disappointed that she wasn't more like Marilyn Monroe. Often I wish I had borrowed my brothers Polaroid camera and gotten a few keepsakes.

OK, now some other details. Gary's house was a very old brick and stone house, probably built before the turn of the century. The main part of the house was one very large open room with a sun room attached to the end. The upstairs covered about half of the area with a balcony overlooking the livingroom, the dining area under the balcony and two bedrooms above the sun room. The kitchen had been a separate building but a hallway with a master bedroom suite off to the side now connected it to the house. There was also a large smoke house about 30 feet from the door into the kitchen and this had been converted into another small house—a bedroom and a bath—this was Gary's room. The basement had been converted into a family room, a one car garage (the house was on the side of a steep hill overlooking a creek) and a room where Gary's father had built a huge model railroad.

Needless to say, having a separate house was great for sneaking girls in or having parties after the parents had gone to bed—and Gary and Margret (her house was only a hundred yards away through the woods) spent a lot of time in there that the parents didn't know about.

As for me and Bridgett, I had my own nice circumstance. At the time, my mother was a teacher at the same school I went to. This meant that, most days, I'd drive her to work, getting to school really early, and then take the car after school with instructions to return to pick her up. School was out at 3:15 and rarely did mom want to be picked up before 5:30—usually at six. Both of my brothers had graduated and were in college and my dad usually didn't get home until 6 or 6:30. I reliably had the house to myself for a couple of hours every day.

Well, one Friday night the four of us decided to go to the local drive in. This time we were in my parents Country Squire wagon (remember those big Fords with the fake wood on the sides?). As the show started (Play it Again Sam, I've always been a Woody Allen fan) Bridgett and I were cuddled up on the right side of the front seat and Gary and Margret were on the left side of the back seat. It wasn't long before I had my hand up Bridgett's shirt (she had left the training bra at home) while Gary was working Margret's pants down around her hips. Bridgett was wearing a skirt and pretty soon her panties were around one of her ankles and my finger was inside her pussy. I looked over the seat, Margret was giving Gary a blow job. I unzipped and Bridgett stroked me (she just shook her head when I nodded down at my cock). We were all brought back to reality when Margret started to laugh. The windows were completely fogged except where Gary's spunk had hit the left side backseat window and my goo was running over Bridgett's hands. At that point the laughing girls took a trip to the ladies room and left us to clean up the car. If I remember correctly, it was one day the following week that I met Bridgett's bus after school and we drove to my house.

I got us something to drink (I'm not sure what, my Mom never kept Coke or anything like that in the house) and it wasn't long before we were both naked on the couch in the living room (under the bay window). I didn't have any rubbers so I didn't even try to fuck her (I was a virgin then too) but we ended up doing 'frontage', me on top sliding my hard-on along her slit and stomach. I really slimed up her belly and chest, some of my cum hit her shoulder, and she giggled as she pushed me away. She sat up quick and pushed a few drops up her stomach, away from her pussy. “Well, get some paper towel!” she said as she made sure my sperm hadn't gotten anyplace near her crack. Today, I cherish the image of the eleven year old with her front all gooey with my sperm. Unfortunately, she caught hell for not checking in at home after school before going to a 'friends' house and was on restriction for a week—no double date that weekend and no visits from me, only a couple very short phone calls.

Finally, almost two weeks later, the four of us were out on the town again. This time we ended up wondering around the Mall in Washington. We were in the woods that are on the north side of the reflecting pool (where the Viet Nam Memorial is now), and Bridgett and I were rolling around in the leaves. It had cooled off quite a bit, we were both wearing jackets and the like, but I had my hand down her pants and she was stroking my cock with cool hands. I ended up spraying my spunk all over the front of my jacket. When I came I pushed two fingers hard into her and she sort of hissed and pushed my hand away, then rolled away from me. I remember holding my hand up in the dim light and seeing that it was sticky and dark. I didn't realize what had happened until a few minutes later when we went back onto a walkway and I saw that there was blood on my fingers. Stupid me, at first I thought she was having a period until she made the wry comment that “she couldn't call herself a virgin anymore.”

I seem to remember that it was just the following night that we actually did it. It was up in my bedroom, missionary style, with a rubber, and short. From then on we were fucking like rabbits every day after school. The memories of watching my rubber encased cock slide in and out of that hairless pussy have lasted me a life time—never since have I had the opportunity to relive those times.

Well, all good things must come to an end. One evening Gary and Margret got busted out in his little house. In the ensuing row Mrs. Van Westhous put two and two together—some close questioning of Bridgett about what she knew about her brother. It was normal for Mrs. Van Westhous and my mom to talk a lot on the phone, it was not normal for me to be summoned to my parents bedroom after they hung up.

Needless to say, the double dates ended and I was under strict orders not to be alone with Bridgett anymore. Several years later, after I was married and she was still in college, we ran into each other and shared a cup of coffee at a Denny's. We laughed some about the antics that went on and hugged when we parted. At one point she said, “I know I wasn't in love with you but I don't regret what we did. I grew up a lot that year.” At least I know that there are no hard feelings (pun intended).